Identification

Name
Mycophenolate mofetil
Accession Number
DB00688
Description

Mycophenolate mofetil, also known as MMF or CellCept, is a prodrug of mycophenolic acid, and classified as a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH).3 This drug is an immunosuppressant combined with drugs such as Cyclosporine and corticosteroids to prevent organ rejection after hepatic, renal, and cardiac transplants.13 It is marketed by Roche Pharmaceuticals and was granted FDA approval for the prophylaxis of transplant rejection in 1995.6 In addition to the above uses, mycophenolate mofetil has also been studied for the treatment of nephritis and other complications of autoimmune diseases. Unlike another immunosuppressant class, the calcineurin inhibitors, MMF generally does not cause nephrotoxicity or fibrosis.2,3

Previously, mycophenolic acid (MPA) was administered to individuals with autoimmune diseases beginning in the 1970s, but was discontinued due to gastrointestinal effects and concerns over carcinogenicity.6 The new semi-synthetic 2-morpholinoethyl ester of MPA was synthesized to avoid the gastrointestinal effects associated with the administration of MPA. It demonstrates an increased bioavailability, a higher efficacy, and reduced gastrointestinal effects when compared to MPA.6

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 433.4947
Monoisotopic: 433.210052351
Chemical Formula
C23H31NO7
Synonyms
  • 2-morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate
  • Mycophenolate mofetil
  • Mycophenolic acid morpholinoethyl ester
External IDs
  • 168396
  • RS 61443
  • RS-61443

Pharmacology

Indication

Mycophenolate mofetil is indicated for the prophylaxis of organ rejection in patients undergoing allogeneic renal, hepatic, or cardiac transplants. It should be used with cyclosporine and corticosteroids.13 Mycophenolate mofetil may also be used off-label as a second-line treatment for autoimmune hepatitis that has not responded adequately to first-line therapy.4 Other off-label uses of this drug include lupus-associated nephritis and dermatitis in children.5

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Mycophenolate mofetil is a prodrug of mycophenolic acid (MPA). The active form of mycophenolate, MPA, prevents the proliferation of immune cells and the formation of antibodies that cause transplant rejection.3 The above effects lead to higher rates of successful transplantation, avoiding the devastating effects of graft rejection.

Mechanism of action

The active metabolite of mycophenolate, mycophenolic acid, prevents T-cell and B-cell proliferation and the production of cytotoxic T-cells and antibodies. Lymphocyte and monocyte adhesion to endothelial cells of blood vessels that normally part of inflammation is prevented via the glycosylation of cell adhesion molecules by MPA.9 MPA inhibits de novo purine biosynthesis (that promotes immune cell proliferation) by inhibiting inosine 5’-monophosphate dehydrogenase enzyme (IMPDH), with a preferential inhibition of IMPDH II.6 IMPDH normally transforms inosine monophosphate (IMP) to xanthine monophosphate (XMP), a metabolite contributing to the production of guanosine triphosphate (GTP).2,3,5 GTP is an important molecule for the synthesis of ribonucleic acid (RNA), deoxyribonucleic acid (DNA), and protein. As a result of the above cascade of effects, mycophenolate mofetil reduces de-novo production of guanosine nucleotides, interfering with the synthesis of DNA, RNA, and protein required for immune cell production.6 Further contributing to the above anti-inflammatory effects, MMF depletes tetrahydrobiopterin, causing the decreased function of inducible nitric oxide synthase enzyme, in turn decreasing the production of peroxynitrite, a molecule that promotes inflammation.12

TargetActionsOrganism
AInosine-5'-monophosphate dehydrogenase 1
inhibitor
inducer
Humans
AInosine-5'-monophosphate dehydrogenase 2
inhibitor
Humans
U6-pyruvoyl tetrahydrobiopterin synthase
inhibitor
Humans
Absorption

Mycophenolate mofetil is rapidly absorbed in the small intestine.13,10 The maximum concentration of its active metabolite, MPA, is attained 60 to 90 minutes following an oral dose.6 The average bioavailability of orally administered mycophenolate mofetil in a pharmacokinetic study of 12 healthy patients was 94%. In healthy volunteers, the Cmax of mycophenolate mofetil was 24.5 (±9.5)μg/mL.13 In renal transplant patients 5 days post-transplant, Cmax was 12.0 (±3.82) μg/mL, increasing to 24.1 (±12.1)μg/mL 3 months after transplantation. AUC values were 63.9 (±16.2) μg•h/mL in healthy volunteers after one dose, and 40.8 (±11.4) μg•h/mL, and 65.3 (±35.4)μg•h/mL 5 days and 3 months after a renal transplant, respectively.13 The absorption of mycophenolate mofetil is not affected by food.6

Volume of distribution

The volume of distribution of mycophenolate mofetil is 3.6 (±1.5) to 4.0 (±1.2) L/kg.13

Protein binding

The protein binding of mycophenolic acid, the metabolite of mycophenolate mofetil, is 97%13 and it is mainly bound to albumin.6 MPAG, the inactive metabolite, is 82% bound to plasma albumin at normal therapeutic concentrations. At elevated MPAG concentrations due to various reasons, including renal impairment, the binding of MPA may be decreased due to competition for binding.13

Metabolism

After both oral and intravenous administration mycophenolate mofetil is entirely metabolized by liver carboxylesterases 1 and 2 to mycophenolic acid (MPA), the active parent drug. It is then metabolized by the enzyme glucuronyl transferase, producing the inactive phenolic glucuronide of MPA (MPAG).13 The glucuronide metabolite is important, as it is then converted to MPA through enterohepatic recirculation. Mycophenolate mofetil that escapes metabolism in the intestine enters the liver via the portal vein and is transformed to pharmacologically active MPA in the liver cells.10N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and the N-oxide portion of N-(2-hydroxyethyl)-morpholine are additional metabolites of MMF occurring in the intestine as a result of liver carboxylesterase 2 activity.10,13 UGT1A9 and UGT2B7 in the liver are the major enzymes contributing to the metabolism of MPA in addition to other UGT enzymes, which also play a role in MPA metabolism. The four major metabolites of MPA are 7-O-MPA-β-glucuronide (MPAG, inactive), MPA acyl-glucuronide (AcMPAG), produced by uridine 5ʹ-diphosphate glucuronosyltransferases (UGT) activities, 7-O-MPA glucoside produced via UGT, and small amounts 6-O-des-methyl-MPA (DM-MPA) via CYP3A4/5 and CYP2C8 enzymes.6

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Route of elimination

A small amount of drug is excreted as MPA in the urine (less than 1%). When mycophenolate mofetil was given orally in a pharmacokinetic study, it was found to be 93% excreted in urine and 6% excreted in feces. Approximately 87% of the entire administered dose is found to be excreted in the urine as MPAG, an inactive metabolite.6,13

Half-life

The average apparent half-life of mycophenolate mofetil is 17.9 (±6.5) hours after oral administration and 16.6 (±5.8) hours after intravenous administration.13

Clearance

Plasma clearance of mycophenolate mofetil is 193 mL/min after an oral dose and 177 (±31) mL/min after an intravenous dose.13

Adverse Effects
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Toxicity

LD50

The LD50 of oral mycophenolate mofetil in rats is 250 mg/kg and >4000 mg/kg in mice.14

Overdose information

Possible signs and symptoms of acute overdose may consist of hematological abnormalities including leukopenia and neutropenia, and gastrointestinal symptoms.6,7,8

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Mycophenolic Acid Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirMycophenolate mofetil may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Mycophenolate mofetil can be increased when combined with Abatacept.
AbemaciclibAbemaciclib may decrease the excretion rate of Mycophenolate mofetil which could result in a higher serum level.
AbirateroneThe metabolism of Mycophenolate mofetil can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Mycophenolate mofetil can be decreased when combined with Acalabrutinib.
AcarboseAcarbose may decrease the excretion rate of Mycophenolate mofetil which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Mycophenolate mofetil which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Mycophenolate mofetil which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Mycophenolate mofetil is combined with Acenocoumarol.
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Food Interactions
  • Avoid multivalent ions. Take multivalent ions such as calcium, iron, or magnesium at least 2 hours after taking this medication.
  • Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Mycophenolate mofetil hydrochlorideUXH81S8ZVB116680-01-4OWLCGJBUTJXNOF-HDNKIUSMSA-N
Active Moieties
NameKindUNIICASInChI Key
Mycophenolic acidprodrugHU9DX48N0T24280-93-1HPNSFSBZBAHARI-RUDMXATFSA-N
Product Images
International/Other Brands
CellCept Oral Suspension (Genentech USA, Inc.) / CellCept Intravenous (Genentech USA, Inc.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CellCeptCapsule250 mg/1OralLake Erie Medical DBA Quality Care Products LLC2011-11-292015-12-31US flag
CellceptTablet500 mgOralRoche Registration Gmb H1996-02-14Not applicableEU flag
CellceptCapsule250 mgOralRoche Registration Gmb H1996-02-14Not applicableEU flag
CellCeptInjection, powder, lyophilized, for solution500 mg/20mLIntravenousGenentech, Inc.1998-08-12Not applicableUS flag
CellCeptCapsule250 mg/1OralCardinal Health1995-05-032017-05-31US flag55154 312220180907 15195 1ns7iwa
CellCeptCapsule250 mg/1OralF. Hoffmann-La Roche Ltd1995-05-032010-06-20US flag
CellCeptTablet500 mgOralHoffmann La Roche1998-11-11Not applicableCanada flag
CellceptTablet500 mgOralRoche Registration Gmb H1996-02-14Not applicableEU flag
CellCeptTablet, film coated500 mg/1OralLake Erie Medical DBA Quality Care Products LLC1997-06-192015-12-31US flag00004 0260 01 nlmimage10 5e132f39
CellCeptCapsule250 mg/1OralGenentech, Inc.1995-05-03Not applicableUS flag00004 0259 01 nlmimage10 b8135c6a
Additional Data Available
  • Application Number
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  • Product Code
    Product Code
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-mycophenolate Mofetil CapsulesCapsuleOralAccel Pharma IncNot applicableNot applicableCanada flag
Accel-mycophenolate Mofetil TabletsTabletOralAccel Pharma IncNot applicableNot applicableCanada flag
Ach-mycophenolateCapsuleOralAccord Healthcare Inc2012-05-01Not applicableCanada flag
Ag-mycophenolateTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-mycophenolateTabletOralApotex Corporation2011-12-01Not applicableCanada flag
Apo-mycophenolateCapsuleOralApotex Corporation2011-12-01Not applicableCanada flag
Jamp-mycophenolateTabletOralJamp Pharma Corporation2012-03-23Not applicableCanada flag
Jamp-mycophenolate CapsulesCapsuleOralJamp Pharma Corporation2012-06-13Not applicableCanada flag
Mycophenolate mofetilTablet, film coated500 mg/1OralAv Pak2016-08-252018-04-11US flag
Mycophenolate MofetilTablet, film coated500 mg/1OralCadila Pharnmaceuticals2009-05-04Not applicableUS flag
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  • Product Code
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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phthalides. These are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isocoumarans
Sub Class
Isobenzofuranones
Direct Parent
Phthalides
Alternative Parents
Anisoles / Alkyl aryl ethers / Fatty acid esters / Morpholines / Dicarboxylic acids and derivatives / Vinylogous acids / Trialkylamines / Amino acids and derivatives / Lactones / Carboxylic acid esters
show 7 more
Substituents
Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, carboxylic ester, phenols, ether, gamma-lactone (CHEBI:8764)

Chemical Identifiers

UNII
9242ECW6R0
CAS number
128794-94-5
InChI Key
RTGDFNSFWBGLEC-SYZQJQIISA-N
InChI
InChI=1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+
IUPAC Name
2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
SMILES
COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C

References

Synthesis Reference

Roger C. Fu, De-Mei Leung, Jeffrey S. Fleitman, Michele C. Rizzolio, Andrew R. Miksztal, "Process for preparing pharmaceutical compositions containing crystalline anhydrous mycophenolate mofetil salts." U.S. Patent US5545637, issued November, 1988.

US5545637
General References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183]
  2. Villarroel MC, Hidalgo M, Jimeno A: Mycophenolate mofetil: An update. Drugs Today (Barc). 2009 Jul;45(7):521-32. doi: 10.1358/dot.2009.45.7.1384878. [PubMed:19834629]
  3. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [PubMed:15803924]
  4. Santiago P, Schwartz I, Tamariz L, Levy C: Systematic review with meta-analysis: mycophenolate mofetil as a second-line therapy for autoimmune hepatitis. Aliment Pharmacol Ther. 2019 Apr;49(7):830-839. doi: 10.1111/apt.15157. Epub 2019 Feb 13. [PubMed:30761563]
  5. Sagcal-Gironella AC, Fukuda T, Wiers K, Cox S, Nelson S, Dina B, Sherwin CM, Klein-Gitelman MS, Vinks AA, Brunner HI: Pharmacokinetics and pharmacodynamics of mycophenolic acid and their relation to response to therapy of childhood-onset systemic lupus erythematosus. Semin Arthritis Rheum. 2011 Feb;40(4):307-13. doi: 10.1016/j.semarthrit.2010.05.007. Epub 2010 Jul 23. [PubMed:20655577]
  6. Park H: The emergence of mycophenolate mofetilin dermatology: from its roots in the world of organ transplantation to its versatile role in the dermatology treatment room. J Clin Aesthet Dermatol. 2011 Jan;4(1):18-27. [PubMed:21278895]
  7. Alex R, Mathew M, Arul S, Kundavaram A: Overdose of mycophenolate mofetil managed in a secondary care hospital in South India. Indian J Pharmacol. 2014 May-Jun;46(3):337-8. doi: 10.4103/0253-7613.132191. [PubMed:24987184]
  8. Parfitt JR, Jayakumar S, Driman DK: Mycophenolate mofetil-related gastrointestinal mucosal injury: variable injury patterns, including graft-versus-host disease-like changes. Am J Surg Pathol. 2008 Sep;32(9):1367-72. [PubMed:18763324]
  9. Allison AC, Eugui EM: Purine metabolism and immunosuppressive effects of mycophenolate mofetil (MMF). Clin Transplant. 1996 Feb;10(1 Pt 2):77-84. [PubMed:8680053]
  10. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
  11. Sherwin CM, Fukuda T, Brunner HI, Goebel J, Vinks AA: The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24. doi: 10.2165/11536640-000000000-00000. [PubMed:21142265]
  12. Srinivas TR, Kaplan B, Meier-Kriesche HU: Mycophenolate mofetil in solid-organ transplantation. Expert Opin Pharmacother. 2003 Dec;4(12):2325-45. doi: 10.1517/14656566.4.12.2325 . [PubMed:14640931]
  13. FDA label, Mycophenolate mofetil [Link]
  14. MSDS, Mycophenolate mofetil [Link]
Human Metabolome Database
HMDB0014826
KEGG Drug
D00752
KEGG Compound
C07908
PubChem Compound
5281078
PubChem Substance
46505626
ChemSpider
4444535
BindingDB
50248299
RxNav
68149
ChEBI
8764
ChEMBL
CHEMBL1456
ZINC
ZINC000021297660
Therapeutic Targets Database
DNC000397
PharmGKB
PA450566
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mycophenolic_acid
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
  • 92:44.00 — Immunosuppressive Agents
FDA label
Download (200 KB)
MSDS
Download (82.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingHealth Services ResearchTransplantation, Liver1
4Active Not RecruitingTreatmentFunction of Renal Transplant1
4Active Not RecruitingTreatmentHepatocellular Carcinoma1
4Active Not RecruitingTreatmentKidney Transplant Patients1
4CompletedNot AvailableAcute Rejection of Renal Transplant1
4CompletedNot AvailableEnd Stage Renal Disease (ESRD)1
4CompletedDiagnosticCardiac Transplant1
4CompletedPreventionAdverse Effects / Transplantation, Kidney1
4CompletedPreventionCardiac Transplantation1
4CompletedPreventionDisorder Related to Renal Transplantation1

Pharmacoeconomics

Manufacturers
  • Roche palo alto llc
  • Accord healthcare inc usa
  • Apotex corp
  • Endo pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Sandoz inc
  • Strides arcolab ltd
  • Teva pharmaceuticals usa
  • Zydus pharmaceuticals usa inc
  • Accord healthcare inc
  • Apotex inc
Packagers
  • Accord Healthcare
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Cadila Healthcare Ltd.
  • Cardinal Health
  • Chunghwa Chemical Synthesis and Biotech Co. Ltd.
  • Endo Pharmaceuticals Inc.
  • F Hoffmann La Roche Ltd.
  • F Hoffmann-La Roche Ltd.
  • Intas Pharmaceuticals Ltd.
  • JHP Pharmaceuticals LLC
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Legacy Pharmaceuticals Packaging LLC
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Poli Industria Chimica SPA
  • Rebel Distributors Corp.
  • Roxane Labs
  • Sandoz
  • Syntex SA
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral180 MG
TabletOral360 MG
CapsuleOral
CapsuleOral250 mg/1
CapsuleOral250 mg
Injection, powder, for solutionIntravenous500 mg
Injection, powder, lyophilized, for solutionIntravenous500 mg/20mL
Powder, for suspensionOral1 g/5ml
Powder, for suspensionOral200 mg
TabletOral500 mg
Tablet, film coatedOral
Tablet, film coatedOral500 mg/1
Injection, solutionIntravenous500 mg
Powder, for solutionIntravenous
Tablet, film coatedOral250 mg
Powder, for suspensionOral200 mg/1mL
TabletOral500 mg/1
Tablet, coatedOral500 mg/1
Tablet, film coatedOral500 mg
Injection, powder, for solutionParenteral500 mg
Tablet, coatedOral500 MG
TabletOral
Prices
Unit descriptionCostUnit
CellCept 200 mg/ml Suspension 175ml Bottle875.84USD bottle
Cellcept 500 mg vial65.03USD vial
Cellcept 500 mg tablet10.43USD tablet
Mycophenolate Mofetil 500 mg tablet8.25USD tablet
Mycophenolate 500 mg tablet7.93USD tablet
CellCept 250 mg capsule5.21USD capsule
Mycophenolate Mofetil 250 mg capsule4.13USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5688529No1997-11-182014-11-18US flag
US5543408No1996-08-062013-09-15US flag
CA2172506No2007-07-172014-09-27Canada flag
CA1333285No1994-11-292011-11-29Canada flag
Additional Data Available
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    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)93-94https://pubchem.ncbi.nlm.nih.gov/compound/Mycophenolate-mofetil#section=Experimental-Properties
boiling point (°C)637.6±55.0http://www.chemspider.com/Chemical-Structure.4444535.html
water solubility43 μg/mL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050722s021,050723s019,050758s019,050759s024lbl.pdf
logP2.5http://www.hmdb.ca/metabolites/HMDB0014826
pKa5.6 for the morpholino group and 8.5 for the phenolic grouphttps://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050722s021,050723s019,050758s019,050759s024lbl.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.095 mg/mLALOGPS
logP2.17ALOGPS
logP3.47ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)6.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.53 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.1 m3·mol-1ChemAxon
Polarizability45.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8938
Blood Brain Barrier+0.8594
Caco-2 permeable+0.5904
P-glycoprotein substrateSubstrate0.8908
P-glycoprotein inhibitor IInhibitor0.8381
P-glycoprotein inhibitor IIInhibitor0.8061
Renal organic cation transporterInhibitor0.5379
CYP450 2C9 substrateNon-substrate0.8528
CYP450 2D6 substrateNon-substrate0.602
CYP450 3A4 substrateSubstrate0.7646
CYP450 1A2 substrateNon-inhibitor0.6878
CYP450 2C9 inhibitorNon-inhibitor0.9155
CYP450 2D6 inhibitorNon-inhibitor0.7684
CYP450 2C19 inhibitorNon-inhibitor0.9122
CYP450 3A4 inhibitorNon-inhibitor0.8316
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8664
Ames testNon AMES toxic0.6484
CarcinogenicityNon-carcinogens0.953
BiodegradationNot ready biodegradable0.658
Rat acute toxicity3.0412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.771
hERG inhibition (predictor II)Non-inhibitor0.7653
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0019-1741900000-022d7009668cda105e50

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Inducer
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH1
Uniprot ID
P20839
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 1
Molecular Weight
55405.365 Da
References
  1. Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [PubMed:17463174]
  2. Wang J, Yang JW, Zeevi A, Webber SA, Girnita DM, Selby R, Fu J, Shah T, Pravica V, Hutchinson IV, Burckart GJ: IMPDH1 gene polymorphisms and association with acute rejection in renal transplant patients. Clin Pharmacol Ther. 2008 May;83(5):711-7. Epub 2007 Sep 12. [PubMed:17851563]
  3. Sanquer S, Maison P, Tomkiewicz C, Macquin-Mavier I, Legendre C, Barouki R, Lang P: Expression of inosine monophosphate dehydrogenase type I and type II after mycophenolate mofetil treatment: a 2-year follow-up in kidney transplantation. Clin Pharmacol Ther. 2008 Feb;83(2):328-35. Epub 2007 Aug 22. [PubMed:17713475]
  4. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [PubMed:15803924]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna binding
Specific Function
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...
Gene Name
IMPDH2
Uniprot ID
P12268
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 2
Molecular Weight
55804.495 Da
References
  1. Vannozzi F, Filipponi F, Di Paolo A, Danesi R, Urbani L, Bocci G, Catalano G, De Simone P, Mosca F, Del Tacca M: An exploratory study on pharmacogenetics of inosine-monophosphate dehydrogenase II in peripheral mononuclear cells from liver-transplant recipients. Transplant Proc. 2004 Nov;36(9):2787-90. [PubMed:15621150]
  2. Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [PubMed:17463174]
  3. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [PubMed:15803924]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tet...
Gene Name
PTS
Uniprot ID
Q03393
Uniprot Name
6-pyruvoyl tetrahydrobiopterin synthase
Molecular Weight
16385.63 Da
References
  1. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [PubMed:15803924]
  2. Allison AC, Eugui EM: Mycophenolate mofetil and its mechanisms of action. Immunopharmacology. 2000 May;47(2-3):85-118. [PubMed:10878285]
  3. Srinivas TR, Kaplan B, Meier-Kriesche HU: Mycophenolate mofetil in solid-organ transplantation. Expert Opin Pharmacother. 2003 Dec;4(12):2325-45. doi: 10.1517/14656566.4.12.2325 . [PubMed:14640931]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A7
Uniprot ID
Q9HAW7
Uniprot Name
UDP-glucuronosyltransferase 1-7
Molecular Weight
59818.315 Da
References
  1. Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
Gene Name
UGT1A6
Uniprot ID
P19224
Uniprot Name
UDP-glucuronosyltransferase 1-6
Molecular Weight
60750.215 Da
References
  1. Miles KK, Kessler FK, Smith PC, Ritter JK: Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. Epub 2006 Jun 21. [PubMed:16790558]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Picard N, Ratanasavanh D, Premaud A, Le Meur Y, Marquet P: Identification of the UDP-glucuronosyltransferase isoforms involved in mycophenolic acid phase II metabolism. Drug Metab Dispos. 2005 Jan;33(1):139-46. Epub 2004 Oct 6. [PubMed:15470161]
  2. Sherwin CM, Fukuda T, Brunner HI, Goebel J, Vinks AA: The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24. doi: 10.2165/11536640-000000000-00000. [PubMed:21142265]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Picard N, Ratanasavanh D, Premaud A, Le Meur Y, Marquet P: Identification of the UDP-glucuronosyltransferase isoforms involved in mycophenolic acid phase II metabolism. Drug Metab Dispos. 2005 Jan;33(1):139-46. Epub 2004 Oct 6. [PubMed:15470161]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A8
Uniprot ID
Q9HAW9
Uniprot Name
UDP-glucuronosyltransferase 1-8
Molecular Weight
59741.035 Da
References
  1. Thervet E, Anglicheau D, Legendre C: [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7. [PubMed:11817210]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein kinase c binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A10
Uniprot ID
Q9HAW8
Uniprot Name
UDP-glucuronosyltransferase 1-10
Molecular Weight
59809.075 Da
References
  1. Thervet E, Anglicheau D, Legendre C: [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7. [PubMed:11817210]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Fujiyama N, Miura M, Kato S, Sone T, Isobe M, Satoh S: Involvement of carboxylesterase 1 and 2 in the hydrolysis of mycophenolate mofetil. Drug Metab Dispos. 2010 Dec;38(12):2210-7. doi: 10.1124/dmd.110.034249. Epub 2010 Sep 7. [PubMed:20823294]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [PubMed:15570183]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Not Available
Specific Function
Hydrolase activity
Gene Name
CES2
Uniprot ID
Q6IPK9
Uniprot Name
Carboxylic ester hydrolase
Molecular Weight
64822.895 Da
References
  1. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
  2. Fujiyama N, Miura M, Kato S, Sone T, Isobe M, Satoh S: Involvement of carboxylesterase 1 and 2 in the hydrolysis of mycophenolate mofetil. Drug Metab Dispos. 2010 Dec;38(12):2210-7. doi: 10.1124/dmd.110.034249. Epub 2010 Sep 7. [PubMed:20823294]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Miura M, Satoh S, Inoue K, Kagaya H, Saito M, Inoue T, Suzuki T, Habuchi T: Influence of SLCO1B1, 1B3, 2B1 and ABCC2 genetic polymorphisms on mycophenolic acid pharmacokinetics in Japanese renal transplant recipients. Eur J Clin Pharmacol. 2007 Dec;63(12):1161-9. Epub 2007 Sep 29. [PubMed:17906856]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
  3. Picard N, Yee SW, Woillard JB, Lebranchu Y, Le Meur Y, Giacomini KM, Marquet P: The role of organic anion-transporting polypeptides and their common genetic variants in mycophenolic acid pharmacokinetics. Clin Pharmacol Ther. 2010 Jan;87(1):100-8. doi: 10.1038/clpt.2009.205. Epub 2009 Nov 4. [PubMed:19890249]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Miura M, Satoh S, Inoue K, Kagaya H, Saito M, Inoue T, Suzuki T, Habuchi T: Influence of SLCO1B1, 1B3, 2B1 and ABCC2 genetic polymorphisms on mycophenolic acid pharmacokinetics in Japanese renal transplant recipients. Eur J Clin Pharmacol. 2007 Dec;63(12):1161-9. Epub 2007 Sep 29. [PubMed:17906856]
  2. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [PubMed:24220207]
  3. Picard N, Yee SW, Woillard JB, Lebranchu Y, Le Meur Y, Giacomini KM, Marquet P: The role of organic anion-transporting polypeptides and their common genetic variants in mycophenolic acid pharmacokinetics. Clin Pharmacol Ther. 2010 Jan;87(1):100-8. doi: 10.1038/clpt.2009.205. Epub 2009 Nov 4. [PubMed:19890249]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Miura M, Kagaya H, Satoh S, Inoue K, Saito M, Habuchi T, Suzuki T: Influence of drug transporters and UGT polymorphisms on pharmacokinetics of phenolic glucuronide metabolite of mycophenolic acid in Japanese renal transplant recipients. Ther Drug Monit. 2008 Oct;30(5):559-64. doi: 10.1097/FTD.0b013e3181838063. [PubMed:18695635]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Miura M, Kagaya H, Satoh S, Inoue K, Saito M, Habuchi T, Suzuki T: Influence of drug transporters and UGT polymorphisms on pharmacokinetics of phenolic glucuronide metabolite of mycophenolic acid in Japanese renal transplant recipients. Ther Drug Monit. 2008 Oct;30(5):559-64. doi: 10.1097/FTD.0b013e3181838063. [PubMed:18695635]
  2. Wang J, Figurski M, Shaw LM, Burckart GJ: The impact of P-glycoprotein and Mrp2 on mycophenolic acid levels in mice. Transpl Immunol. 2008 Jul;19(3-4):192-6. doi: 10.1016/j.trim.2008.05.009. Epub 2008 Jun 18. [PubMed:18586494]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Wang J, Figurski M, Shaw LM, Burckart GJ: The impact of P-glycoprotein and Mrp2 on mycophenolic acid levels in mice. Transpl Immunol. 2008 Jul;19(3-4):192-6. doi: 10.1016/j.trim.2008.05.009. Epub 2008 Jun 18. [PubMed:18586494]
  2. Kobayashi M, Saitoh H, Kobayashi M, Tadano K, Takahashi Y, Hirano T: Cyclosporin A, but not tacrolimus, inhibits the biliary excretion of mycophenolic acid glucuronide possibly mediated by multidrug resistance-associated protein 2 in rats. J Pharmacol Exp Ther. 2004 Jun;309(3):1029-35. doi: 10.1124/jpet.103.063073. Epub 2004 Feb 20. [PubMed:14978191]

Drug created on June 13, 2005 07:24 / Updated on November 25, 2020 08:52

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